CA2468658C - Antagonistes du recepteur a<sb>2a</sb> d'adenosine bicyclique de [1,2,4]-triazole - Google Patents

Antagonistes du recepteur a<sb>2a</sb> d'adenosine bicyclique de [1,2,4]-triazole Download PDF

Info

Publication number
CA2468658C
CA2468658C CA002468658A CA2468658A CA2468658C CA 2468658 C CA2468658 C CA 2468658C CA 002468658 A CA002468658 A CA 002468658A CA 2468658 A CA2468658 A CA 2468658A CA 2468658 C CA2468658 C CA 2468658C
Authority
CA
Canada
Prior art keywords
alkyl
concentrate
compound
product
add
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CA002468658A
Other languages
English (en)
Other versions
CA2468658A1 (fr
Inventor
Bernard R. Neustadt
Hong Liu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Sharp and Dohme LLC
Original Assignee
Schering Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Schering Corp filed Critical Schering Corp
Publication of CA2468658A1 publication Critical patent/CA2468658A1/fr
Application granted granted Critical
Publication of CA2468658C publication Critical patent/CA2468658C/fr
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Landscapes

  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Psychiatry (AREA)
  • Hospice & Palliative Care (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Pain & Pain Management (AREA)
  • Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

L'invention concerne des composés de formule structurelle (I), dans laquelle n est un nombre entier 0, 1, 2 ou 3, A représente C(R?1¿) ou N, R?1¿ et R?1a¿ représentent l'hydrogène, (C¿1?-C¿6?)-alkyle, halo, CN ou -CF¿3?; X représente -C(O)-, -O-, - SO¿0-2?- ou un méthylène, un imino, un arylène ou un hétéroaryldiyl facultativement substitué, Y représente O-, -SO¿0-2?- ou un arylène, un hétéroaryldiyle ou un hétérocycloalkyle contenant de l'azote facultativement substitué ou dans certaines conditions, une liaison, R représente un aryle ou un hétéroaryle facultativement substitué, et R?2¿ représente un aryle, un hétéroaryle, un arylalkyle ou un hétéroarylalkyle facultativement substitué ou R?2¿-Y représente un piperidinyl fusionné, un piperazinyl substituté ou un piperidinyl substitué. Cette invention a aussi pour objet l'utilisation de ces composés dans le traitement de la maladie de Parkinson, seuls ou combinés à d'autres agents permettant de traiter la maladie de Parkinson, des compositions pharmaceutiques les contenant, et des kits comprenant les composés de ces combinaisons.
CA002468658A 2001-11-30 2002-11-26 Antagonistes du recepteur a<sb>2a</sb> d'adenosine bicyclique de [1,2,4]-triazole Expired - Fee Related CA2468658C (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US33438501P 2001-11-30 2001-11-30
US60/334,385 2001-11-30
PCT/US2002/037915 WO2003048163A1 (fr) 2001-11-30 2002-11-26 Antagonistes du recepteur a2a d'adenosine bicyclique de [1,2,4]-triazole

Publications (2)

Publication Number Publication Date
CA2468658A1 CA2468658A1 (fr) 2003-06-12
CA2468658C true CA2468658C (fr) 2009-04-14

Family

ID=23306955

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002468658A Expired - Fee Related CA2468658C (fr) 2001-11-30 2002-11-26 Antagonistes du recepteur a<sb>2a</sb> d'adenosine bicyclique de [1,2,4]-triazole

Country Status (18)

Country Link
US (2) US6875772B2 (fr)
EP (1) EP1453836B1 (fr)
JP (2) JP4429724B2 (fr)
KR (1) KR20050044600A (fr)
CN (1) CN1688581A (fr)
AR (1) AR037681A1 (fr)
AT (1) ATE358130T1 (fr)
AU (1) AU2002352933A1 (fr)
CA (1) CA2468658C (fr)
DE (1) DE60219196T2 (fr)
ES (1) ES2283625T3 (fr)
HU (1) HUP0402324A3 (fr)
IL (1) IL161573A0 (fr)
MX (1) MXPA04005158A (fr)
PE (1) PE20030653A1 (fr)
TW (1) TW200300689A (fr)
WO (1) WO2003048163A1 (fr)
ZA (1) ZA200404168B (fr)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL161573A0 (en) * 2001-11-30 2004-09-27 Schering Corp [1,2,4]-TRIAZOLE BICYCLIC ADENOSINE A2a RECEPTOR ANTAGONISTS
AR038366A1 (es) 2001-11-30 2005-01-12 Schering Corp Compuestos de 1,2,4-triazolo [1,5-c] pirimidinas sustituidas, antagonistas del receptor de adenosina a2a, composiciones farmaceuticas, el uso de dichos compuestos para la manufactura de un medicamento para el tratamiento de enfermedades del sistema nervioso central y un kit que comprende combinacion
BR0308347A (pt) * 2002-03-12 2005-01-25 Wyeth Corp Processo para fabricação de piperazinas 1,4-dissubstituìdas quirais
WO2004029056A1 (fr) * 2002-09-24 2004-04-08 Kyowa Hakko Kogyo Co., Ltd. Dérivé de [1,2,4]-triazolo[1,5]pyrimidine
TWI331036B (en) * 2002-12-19 2010-10-01 Schering Corp Adenosine a2a receptor antagonists for the treatment of extra-pyramidal syndrome and other movement disorders
WO2004092177A1 (fr) 2003-04-09 2004-10-28 Biogen Idec Ma Inc. Triazolopyrazines et procedes de preparation et d'utilisation ce celles-ci
WO2004092173A2 (fr) 2003-04-09 2004-10-28 Biogen Idec Ma Inc. Antagonistes de recepteur d'adenosine a2a
WO2004092172A2 (fr) * 2003-04-09 2004-10-28 Biogen Idec Ma Inc. Triazolo[1,5-c]pyrimidines et pyrazolo[1,5-c]pyrimidines et procedes de preparation et d'utilisation de celles-ci
WO2004092170A2 (fr) 2003-04-09 2004-10-28 Biogen Idec Ma Inc. Triazolotriazines et pyrazolotriazines et leurs procedes de fabrication et d'utilisation
TW200507850A (en) * 2003-07-25 2005-03-01 Kyowa Hakko Kogyo Kk Pharmaceutical composition
WO2006129626A1 (fr) * 2005-05-30 2006-12-07 Kyowa Hakko Kogyo Co., Ltd. Procede de fabrication d'un derive de [1,2,4]triazolo[1,5-c]pyrimidine
EP2258372B8 (fr) 2005-06-07 2012-12-19 Kyowa Hakko Kirin Co., Ltd. L'utilisation des antagonistes des récepteurs A2A pour le treaitment de troubles de motricité
US20090124663A1 (en) * 2005-06-08 2009-05-14 Neurosearch A/S Novel n-phenyl-piperidine derivatives and their use as monoamine neurotransmitter re-uptake inhibitors
TW200803856A (en) 2005-09-02 2008-01-16 Mount Cook Biosciences Inc Method of treating parkinson's disease with diarylmethylpiperazine compounds exhibiting delta receptor agonist activity
ES2273599B1 (es) 2005-10-14 2008-06-01 Universidad De Barcelona Compuestos para el tratamiento de la fibrilacion auricular.
US7615556B2 (en) * 2006-01-27 2009-11-10 Bristol-Myers Squibb Company Piperazinyl derivatives as modulators of chemokine receptor activity
EP2274007B1 (fr) 2008-03-10 2016-12-14 Cornell University Modulation de la perméabilité d'une barrière hématoencéphalique
WO2010008775A1 (fr) * 2008-06-23 2010-01-21 Ligand Pharmaceuticals Inc. Dérivés d'aminopyridopyrazinone pour le traitement de maladies neurodégénératives
GB201214106D0 (en) * 2012-08-07 2012-09-19 Univ Strathclyde Immunomodulatory compounds
EP3436013A4 (fr) 2016-03-31 2019-11-13 Versi Group, LLC Compositions à base d'un agoniste du récepteur aux opiacés delta / antagoniste du récepteur aux opiacés mu, et procédés de traitement de la maladie de parkinson
CN106866582A (zh) * 2017-01-10 2017-06-20 广州隽沐生物科技有限公司 一种氟班色林中间体的制备方法
KR102633145B1 (ko) * 2018-06-26 2024-02-05 쩌지앙 빔그린 파머슈티컬스, 엘티디 A2a 수용체 길항제로서의 트리아졸로 트리아진 유도체
WO2020227156A1 (fr) * 2019-05-03 2020-11-12 Nektar Therapeutics Antagonistes du récepteur de l'adénosine 2
JP2023508182A (ja) * 2019-12-26 2023-03-01 チェジン ヴィムグリーン ファーマシューティカルズ リミテッド トリアゾロトリアジン誘導体の疾患治療への応用
MX2023012338A (es) * 2021-04-23 2023-10-30 Chong Kun Dang Pharmaceutical Corp Compuesto como antagonista del receptor de adenosina a2a y composicion farmaceutica que comprende al mismo.

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1264901B1 (it) 1993-06-29 1996-10-17 Schering Plough S P A Analoghi eterociclici di 1,2,4-triazolo(15-c)pirimidine ad attivita' antagonista per il recettore a2 dell'adenosina
WO1995003806A1 (fr) * 1993-07-27 1995-02-09 Kyowa Hakko Kogyo Co., Ltd. Remede contre la maladie de parkinson
IT1277392B1 (it) 1995-07-28 1997-11-10 Schering Plough S P A Analoghi eterociclici di 1,2,4-triazolo(1,5-c]pirimidine ad attivita' antagonista per il recettore a2a dell'adenosina
DE69820866T2 (de) * 1997-03-24 2004-12-30 Kyowa Hakko Kogyo Co., Ltd. [1,2,4]TRIAZOLO[1,5-c]PYRIMIDIN-DERIVATE
IT1291372B1 (it) 1997-05-21 1999-01-07 Schering Plough S P A Uso di analoghi eterociclici di 1,2,4-triazolo (1,5-c) pirimidine per la preparazione di medicamenti utili per il trattamento delle malattie
AU2639299A (en) * 1998-02-24 1999-09-15 Kyowa Hakko Kogyo Co. Ltd. Remedies/preventives for parkinson's disease
WO2000017201A1 (fr) * 1998-09-22 2000-03-30 Kyowa Hakko Kogyo Co., Ltd. DERIVES DE [1,2,4]TRIAZOLO[1,5-c]PYRIMIDINE
US6355653B1 (en) 1999-09-06 2002-03-12 Hoffmann-La Roche Inc. Amino-triazolopyridine derivatives
JP2002037787A (ja) * 2000-05-16 2002-02-06 Kyowa Hakko Kogyo Co Ltd ［１，２，４］トリアゾロ［１，５−ｃ］ピリミジン誘導体の製造法
DE60110219T2 (de) 2000-05-26 2006-03-09 Schering Corp. Adenosin a2a rezeptor antagonisten
KR100687954B1 (ko) * 2001-10-15 2007-02-27 쉐링 코포레이션 아데노신 Ａ2ａ 수용체 길항제로서의이미다조（4,3-ｅ）-1,2,4-트리아졸로（1,5-ｃ） 피리미딘
IL161573A0 (en) * 2001-11-30 2004-09-27 Schering Corp [1,2,4]-TRIAZOLE BICYCLIC ADENOSINE A2a RECEPTOR ANTAGONISTS

Also Published As

Publication number Publication date
JP4429724B2 (ja) 2010-03-10
US20030191130A1 (en) 2003-10-09
KR20050044600A (ko) 2005-05-12
ES2283625T3 (es) 2007-11-01
JP2005511697A (ja) 2005-04-28
TW200300689A (en) 2003-06-16
AU2002352933A1 (en) 2003-06-17
CN1688581A (zh) 2005-10-26
HK1064097A1 (en) 2005-01-21
DE60219196D1 (de) 2007-05-10
EP1453836B1 (fr) 2007-03-28
MXPA04005158A (es) 2004-08-11
HUP0402324A2 (hu) 2005-02-28
PE20030653A1 (es) 2003-08-04
US7078408B2 (en) 2006-07-18
WO2003048163A1 (fr) 2003-06-12
ATE358130T1 (de) 2007-04-15
IL161573A0 (en) 2004-09-27
JP2010018634A (ja) 2010-01-28
HUP0402324A3 (en) 2008-09-29
AR037681A1 (es) 2004-12-01
US6875772B2 (en) 2005-04-05
EP1453836A1 (fr) 2004-09-08
US20050113380A1 (en) 2005-05-26
ZA200404168B (en) 2005-09-02
CA2468658A1 (fr) 2003-06-12
DE60219196T2 (de) 2008-01-03

Similar Documents

Publication Publication Date Title
CA2468658C (fr) Antagonistes du recepteur a&lt;sb&gt;2a&lt;/sb&gt; d&#39;adenosine bicyclique de [1,2,4]-triazole
AU2005236059B2 (en) Pyrazolo-[4,3-e]-1,2,4-triazolo-[1,5-c]-pyrimidine adenosine A2a receptor antagonists
JP4574112B2 (ja) アデノシンａ２ａレセプターアンタゴニスト
JP4284182B2 (ja) アデノシンＡ２ａレセプターアンタゴニスト
EP2282999B1 (fr) Dérivés d&#39;amino-quinoxaline et d&#39;amino-quinoline et leur emploi comme antagonistes du récepteur adenosine a2a
EP1836205B1 (fr) ANTAGONISTES DE RECEPTEUR A2a DE PYRAZOLO [1,5-A]PYRIMIDINE ADENOSINE
HK1064097B (en) Bicyclic [1,2,4] -triazole adenosine a2a receptor antagonists
HK1108882B (en) Pyrazolo[1,5-a]pyrimidine adenosine a2a receptor antagonists
HK1063780B (en) Adenosine a2a receptor antagonists

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20131126